Sulfamoyltriazole derivatives of fungicidal composition containing same as effective component thereof

ABSTRACT

The present invention relates to a sulfamoyl triazole derivative and a fungicide containing same as an effective component, the sulfamoyl triazole derivative being expressed by general formula (I): ##STR1## in which R 1  and R 2  are the same or different lower alkyl groups or an alkylene chain formed by integrating R 1  and R 2  and having 3 to 6 carbon atoms which may be substituted by a lower alkyl group; p is an integer 0 or 1; and A is a substituted aryl group. 
     The fungicide does not damage field and garden plants and it is effective for preventing and curing various disease injury at very small dosages.

FIELD OF INVENTION

The present invention relates to a novel sulfamoyltriazole derivatives and a novel fungicidal composition same as an effective component thereof.

PREVIOUS ART

Japanese Patent Application Laid-Open No. 63-255269 discloses that sulfamoyltriazole derivatives having a specific structure can be used as an effective component of an antifungal agent.

However, the fungicidal activity of the foregoing conventional compounds has been unsatisfactory.

DISCLOSURE OF THE INVENTION

The inventors of the present invention have earnestly studied a variety of substituted sulfamoyltriazole type compounds to develop an agricultural fungicide having high fungicidal activity and excellent safety. As a result, it was found that sulfamoyltriazole derivatives having a triazole ring including a third carbon atom which is substituted by a specific aryl sulfonic group or an aryl oxysulfonic group are novel fungicides which do not damage field and garden plants and which exhibits excellent effects of preventing and curing various disease injury at very small dosages.

(SUMMARY OF THE INVENTION)

According to the present invention, there is provided a sulfamoyltriazole derivative and a fungicide containing same as an effective component thereof, the sulfamoyltriazole derivative being expressed by general formula (I): ##STR2## in which R¹ and R² are the same or different lower alkyl groups or an alkylene chain formed by integrating R¹ and R² and having 3 to 6 carbon atoms which may be substituted by a lower alkyl group; is an integer 0 or 1; and A is expressed by any one of the following substances: ##STR3## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m Is an integer 1, 2, 3, 4 or 5, Y is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; n is an integer 1, 2, 3, 4 or 5; R³ and R⁴ are the same or different hydrogen atoms or lower alkyl groups; and p is an integer 1, 2, 3 or 4.

(CONCRETE DESCRIPTION OF THE INVENTION)

[I] Sulfamoyl Triazole Derivative

The sulfamoyltriazole derivatives according to the present invention and expressed by general formula (I) are described in detail below.

Atoms and groups of the compounds expressed in the general formula (I) expressed by R¹, R², R³, R⁴, X and Y defined as described above are exemplified as follows:

Lower Alkyl Group

A lower alkyl group having one to four carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a secondary butyl group, etc.

Halogen Atom

For example, fluorine, chlorine or bromine.

Lower Alkenyl Group

A lower alkenyl group having two to four carbon atoms such as an allyl group, a 2-methyl-2-propenyl group, a 2-butenyl group, a 3-butenyl group, etc.

Lower Alkoxy Group

A lower alkoxy group having one to four carbon atoms such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a secondary butoxy group, a tert-butoxy group, etc.

Lower Haloalkyl Group

A lower haloalkyl group having one to three carbon atoms such as a dichloromethyl group, a trichloromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-chloroethyl group, a 2-fluoroethyl group, etc.

Lower Haloalkoxy Group

A lower haloalkoxy group having one to three carbon atoms such as a difluoromethoxy group, a trifluoromethoxy group, a 2-chloroethoxy group, 2-2-dichloroethoxy group, a 2,2,2-trichloroethoxy group, a 2-fluoroethoxy group, a 3-bromopropoxy group, etc.

Lower Alkyl Carbonyl Group

A lower alkylcarbonyl group having two to four carbon atoms such as a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, etc.

Lower Alkoxy Carbonyl Group

A lower alkoxycarbonyl group having two to four carbon atoms such as a methoxycarbonyl group, an ethoxy carbonyl group, an n-propoxycarbonyl group, an isopropoxy carbonyl group, etc.

Groups that are not exemplified above may be selected from the foregoing atoms and groups as to be combined arbitrarily or selected according to generally known common sense.

The lower alkyl groups denoted by R¹ and R² in general formula (I) are preferably methyl groups, ethyl groups, n-propyl groups or isopropyl groups.

The lower alkyl groups denoted by R³ and R⁴ are preferably methyl groups, ethyl groups or n-propyl groups.

It is preferable that the halogen atoms denoted by X and Y be fluorine atoms or chlorine atoms, the lower alkyl group be a methyl group, an ethyl group, an n-propyl group or an isopropyl group, the lower haloalkyl group be a trichloromethyl group or a trifluoromethyl group, and the lower haloalkoxy group be a difluoromethoxy group, a trifluoroethoxy group or a tetrafluoroethoxy group. It is preferable that m be 1, 2, 3 or 4, n be 1, 2 or 3 and p be 1, 2 or 3.

It Is preferable that A be the phenyl group substituted by the foregoing substituent, such as a 2,4-dichloro-3-methylphenyl group, a 4-trifluoromethylphenyl group, a 3-chlorophenyl group, a 2,3-dichlorophenyl group, a 2-chloro-4-trifluoromethylphenyl group, a 4-chlorophenyl group and a 3-trifluoromethylphenyl group.

The specific structure of the compounds according to the present invention and expressed by general formula (I) will now be exemplified.

(1) If l in general formula (I) is 1:

(i) General formula (I-1) ##STR4## in which R¹, R², X and m are the same as in general formula (I).

(ii) General Formula (I-2) ##STR5## in which, R¹, R², Y and n are the same as in general formula (I).

(iii) General formula (I-3) ##STR6## in which R¹, R², Y and n are the same as in general formula (I).

(iv) General formula (I-4) ##STR7## in which R¹, R², R³ and R⁴ are the same as in general formula (I).

(v) General formula (I-5) ##STR8## in which R¹, R², R³ and R⁴ are the same as in general formula (I).

(2) If l in general formula (I) is 0:

(vi) General formula (I-6) ##STR9## In which R¹, R², X and m are the same as in general formula (I).

(vii) General formula (I-7) ##STR10## in which R¹, R², Y and n are the same as in general formula (I).

(viii) General formula (I-8) ##STR11## in which R¹, R², Y and n are the same as in general formula (I).

(ix) General formula (I-9) ##STR12## in which R¹, R², R³ and R⁴ are the same as In general formula (I).

(x) General formula (I-10) ##STR13## in which R¹, R², R³ and R⁴ are the same as in general formula (I).

(xi) General formula (I-11) ##STR14## in which X, R¹, R² and p are the same as in general formula (I).

Examples of the compounds expressed by formula (I-1) according to the present invention are shown in Table 1, examples of the compounds expressed by formula (I-2) are shown in Table 2, examples of the compounds expressed by formula (I-3) are shown in Table 3, examples of the compounds expressed by formula (I-4) are shown in Table 4, examples of the compounds expressed by formula (I-5) are shown in Table 5, examples of the compounds expressed by formula (I-6) are shown in Table 6, examples of the compounds expressed by formula (I-7) are shown in Table 7, examples of the compounds expressed by formula (I-8) are shown in Table 8, examples of the compounds expressed by formula (I-9) are shown in Table 9, examples of the compounds expressed by formula (I-10) are shown in Table 10 and examples of the compounds expressed by formula (I-11) are shown in Table 11.

The abbreviations in Tables 1 to 11 respectively denote the following:

Me denotes a methyl group, Et denotes an ethyl group, nPr denotes an n-propyl group, iPr denotes an isopropyl group and tBu denotes a t-butyl group.

                                      TABLE 1                                      __________________________________________________________________________     Compound                                                                       No.   R.sup.1   R.sup.2 X.sub.m                                                __________________________________________________________________________      1    Me        Me      H                                                       2    Me        Et      H                                                       3    Et        Et      H                                                       4    Et        nPr     H                                                       5    Et        iPr     H                                                       6    nPr       nPr     H                                                       7    CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 H                                                       8    CH(Me)-(CH.sub.2).sub.3 CH(Me)-                                                                  H                                                       9    CH(Et)-(CH.sub.2).sub.3 CH.sub.2                                                                 H                                                       10   Me        Me      2-Me                                                    11   Et        Et      2-Me                                                    12   Me        Me      3-Me                                                    13   Et        Et      3-Me                                                    14   Me        Me      4-Me                                                    15   Et        Et      4-Me                                                    16   CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 4-Me                                                    17   Me        Me      2-Et                                                    18   Et        Et      2-Et                                                    19   Me        Me      3-Et                                                    20   Et        Et      3-Et                                                    21   Me        Me      4-Et                                                    22   Et        Et      4-Et                                                    23   Me        Me      2-iPr                                                   24   Et        Et      2-iPr                                                   25   Me        Me      3-iPr                                                   26   Et        Et      3-iPr                                                   27   Me        Me      4-iPr                                                   28   Et        Et      4-iPr                                                   29   Me        Me      4-tBu                                                   30   Et        Et      4-tBu                                                   31   Me        Me      2-F                                                     32   Et        Et      2-F                                                     33   Me        Me      3-F                                                     34   Et        Et      3-F                                                     35   Me        Me      4-F                                                     36   Et        Et      4-F                                                     37   Me        Me      2-Cl                                                    38   Et        Et      2-Cl                                                    39   Me        Me      3-Cl                                                    40   Et        Et      3-Cl                                                    41   Me        Me      4-Cl                                                    42   Et        Et      4-Cl                                                    43   Me        Me      2-Br                                                    44   Et        Et      2-Br                                                    45   Me        Me      2-CH.sub.2 CHCH.sub.2                                   46   Et        Et      2-CH.sub.2 CHCH.sub.2                                   47   Me        Me      2-OMe                                                   48   Et        Et      2-OMe                                                   49   Me        Me      3-OMe                                                   50   Et        Et      3-OMe                                                   51   Me        Me      4-OMe                                                   52   Et        Et      4-OMe                                                   53   Me        Me      3-OEt                                                   54   Et        Et      3-OEt                                                   55   Me        Me      4-OEt                                                   56   Et        Et      4-OEt                                                   57   Me        Me      2-CF.sub.3                                              58   Et        Et      2-CF.sub.3                                              59   Me        Me      3-CF.sub.3                                              60   Et        Et      3-CF.sub.3                                              61   Me        Me      4-CF.sub.3                                              62   Et        Et      4-CF.sub.3                                              63   Me        Me      2-OCHF.sub.2                                            64   Et        Et      2-OCHF.sub.2                                            65   Me        Me      4-OCHF.sub.2                                            66   Et        Et      4-OCHF.sub.2                                            67   Me        Me      2-OCH.sub.2 CF.sub.3                                    68   Et        Et      2-OCH.sub.2 CF.sub.3                                    69   Me        Me      4-OCH.sub.2 CF.sub.3                                    70   Et        Et      4-OCH.sub.2 CF.sub.3                                    71   Me        Me      2-OCF.sub.2 CFClH                                       72   Et        Et      2-OCF.sub.2 CFClH                                       73   Me        Me      2-C.sub.6 H.sub.5                                       74   Et        Et      2-C.sub.6 H.sub.5                                       75   Me        Me      2-CH.sub.2 C.sub.6 H.sub.5                              76   Et        Et      2-CH.sub.2 C.sub.6 H.sub.5                              77   Me        Me      2-OCH.sub.2 C.sub.6 H.sub.5                             78   Et        Et      2-OCH.sub.2 C.sub.6 H.sub.5                             79   Me        Me      2-COCH.sub.3                                            80   Et        Et      2-COCH.sub.3                                            81   Me        Me      2-COOMe                                                 82   Et        Et      2-COOMe                                                 83   Me        Me      4-COOMe                                                 84   Et        Et      4-COOMe                                                 85   Me        Me      2-CHO                                                   86   Et        Et      2-CHO                                                   87   Me        Me      2-NO.sub.2                                              88   Et        Et      2-NO.sub.2                                              89   Me        Me      4-NO.sub.2                                              90   Et        Et      4-NO.sub.2                                              91   Me        Me      2-CN                                                    92   Et        Et      2-CN                                                    93   Me        Me      3-CN                                                    94   Et        Et      3-CN                                                    95   Me        Me      4-CN                                                    96   Et        Et      4-CN                                                    97   Me        Me      2-NHCOCH.sub.3                                          98   Et        Et      2-NHCOCH.sub.3                                          99   Me        Me      4-NHCOCH.sub.3                                         100   Et        Et      4-NHCOCH.sub.3                                         101   Me        Me      2,6-(Me).sub.2                                         102   Me        Et      2,6-(Me).sub.2                                         103   Et        Et      2,6-(Me).sub.2                                         104   Et        nPr     2,6-(Me).sub.2                                         105   Et        iPr     2,6-(Me).sub.2                                         106   nPr       nPr     2,6-(Me).sub.2                                         107   CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 2,6-(Me).sub.2                                         108   Me        Me      2,4-(Me).sub.2                                         109   Et        Et      2,4-(Me).sub.2                                         110   Me        Me      3,4-(Me).sub.2                                         111   Et        Et      3,4-(Me).sub.2                                         112   Me        Me      3,5-(Me).sub.2                                         113   Et        Et      3,5-(Me).sub.2                                         114   Me        Me      2,3-(Me).sub.2                                         115   Et        Et      2,3-(Me).sub.2                                         116   Me        Me      2,6-(Et).sub.2                                         117   Et        Et      2,6-(Et).sub.2                                         118   Me        Me      2-Me-6-Et                                              119   Et        Et      2-Me-6-Et                                              120   Me        Me      2-Me-5-iPr                                             121   Et        Et      2-Me-5-iPr                                             122   Me        Me      2-iPr-5-Me                                             123   Et        Et      2-iPr-5-Me                                             124   Me        Me      2-Me-4-Cl                                              125   Et        Et      2-Me-4-Cl                                              126   Me        Me      2-Me-6-Cl                                              127   Et        Et      2-Me-6-Cl                                              128   Me        Me      3-Me-4-Cl                                              129   Et        Et      3-Me-4-Cl                                              130   Me        Me      2-Me-4-F                                               131   Et        Et      2-Me-4-F                                               132   Me        Mer     2,4-F.sub.2                                            133   Et        Etr     2,4-F.sub. 2                                           134   Me        Me      2,6-F.sub.2                                            135   Et        Et      2,6-F.sub.2                                            136   Me        Me      2,3-Cl.sub.2                                           137   Et        Et      2,3-Cl.sub.2                                           138   Me        Me      2,4-Cl.sub.2                                           139   Et        Et      2,4-Cl.sub.2                                           140   Me        Me      2,5-Cl.sub.2                                           141   Et        Et      2,5-Cl.sub.2                                           142   Me        Me      2,6-Cl.sub.2                                           143   Et        Et      2,6-Cl.sub.2                                           144   Me        Me      2-Cl-4-F                                               145   Et        Et      2-Cl-4-F                                               146   Me        Me      2-Cl-6-F                                               147   Et        Et      2-Cl-6-F                                               148   Me        Me      4-Cl-2-F                                               139   Et        Et      4-Cl-2-F                                               150   Me        Me      2-OMe-4-Me                                             151   Et        Et      2-OMe-4-Me                                             152   Me        Me      2,6-(OMe).sub.2                                        153   Et        Et      2,6-(OMe).sub.2                                        154   Me        Me      2-F-6-OMe                                              155   Et        Et      2-F-6-OMe                                              156   Me        Me      3-Cl-5-OMe                                             157   Et        Et      3-Cl-5-OMe                                             158   Me        Me      2-OMe-4-CHCHCH.sub.3                                   159   Et        Et      2-OMe-4-CHCHCH.sub.3                                   160   Me        m       2-OMe-4-CH.sub.2 CHCH.sub.2                            161   Et        Et      2-OMe-4-CH.sub.2 CHCH.sub.2                            162   Me        Me      3,5-(CF.sub.3).sub.2                                   163   Et        Et      3,5-(CF.sub.3).sub.2                                   164   Me        Me      2-Cl-4-CF.sub.3                                        165   Et        Et      2-Cl-4-CF.sub.3                                        166   Me        Me      2-Cl-5-CF.sub.3                                        167   Et        Et      2-Cl-5-CF.sub.3                                        168   Me        Me      2-Me-6-COOMe                                           169   Et        Et      2-Me-6-COOMe                                           170   Me        Me      2-OMe-6-COOMe                                          171   Et        Et      2-OMe-6-COOMe                                          172   Me        Me      2-Cl-6-COOMe                                           173   Et        Et      2-Cl-6-COOMe                                           174   Me        Me      2-NO.sub.2 -3-Me                                       175   Et        Et      2-NO.sub.2 -3-Me                                       176   Me        Me      2-CN-4-F                                               177   Et        Et      2-CN-4-F                                               178   Me        Me      2-CN-4-Cl                                              179   Et        Et      2-CN-4-Cl                                              180   Me        Me      2-CN-4-Br                                              181   Et        Et      2-CN-4-Br                                              182   Me        Me      4-CN-2-F                                               183   Et        Et      4-CN-2-F                                               184   Me        Me      4-CN-2-Cl                                              185   Et        Et      4-CN-2-Cl                                              186   Me        Me      4-CN-2-Br                                              187   Et        Et      4-CN-2-Br                                              188   Me        Me      2,3,5-(Me).sub.3                                       189   Et        Et      2,3,5-(Me).sub.3                                       190   Me        Me      2,3,6-(Me).sub.3                                       191   Et        Et      2,3,6-(Me).sub.3                                       192   Me        Me      2,4,6-(Me).sub.3                                       193   Me        Et      2,4,6-(Me).sub.3                                       194   Et        Et      2,4,6-(Me).sub.3                                       195   Et        nPr     2,4,6-(Me).sub.3                                       196   Et        iPr     2,4,6-(Me).sub.3                                       197   nPr       nPr     2,4,6-(Me).sub.3                                       198   Me        Me      2,4-(Me).sub.2 -6-Cl                                   199   Et        Et      2,4-(Me).sub.2 -6-Cl                                   200   Me        Me      2,6-(Me).sub.2 -4-Cl                                   201   Et        Et      2,6-(Me).sub.2 -4-Cl                                   202   Me        Me      2,4-Cl.sub.2 -6-Me                                     203   Et        Et      2,4-Cl.sub.2 -6-Me                                     204   Me        Me      2,6-Cl.sub.2 -4-Me                                     205   Et        Et      2,6-Cl.sub.2 -4-Me                                     206   Me        Me      2,4-Cl.sub.2 -3-Me                                     207   Et        Et      2,4-Cl.sub.2 -3-Me                                     208   Me        Me      2,6-Cl.sub.2 -4-CF.sub.3                               209   Et        Et      2,6-Cl.sub.2 -4-CF.sub.3                               210   Me        Me      2,3,4-Cl.sub.3                                         211   Et        Et      2,3,4-Cl.sub.3                                         212   Me        Me      2,3,6-Cl.sub.3                                         213   Et        Et      2,3,6-Cl.sub.3                                         214   Me        Me      2,4,5-Cl.sub.3                                         215   Et        Et      2,4,5-Cl.sub.3                                         216   Me        Me      2,4,6-Cl.sub.3                                         217   Me        Et      2,4,6-Cl.sub.3                                         218   Et        Et      2,4,6-Cl.sub.3                                         219   Et        nPr     2,4,6-Cl.sub.3                                         220   Et        iPr     2,4,6-Cl.sub.3                                         221   nPr       nPr     2,4,6-Cl.sub.3                                         222   Me        Me      3,4,5-(OMe).sub.3                                      223   Et        Et      3,4,5-(OMe).sub.3                                      224   Me        Me      2,4-Cl.sub.2 -6-COOMe                                  225   Et        Et      2,4-Cl.sub.2 -6-COOMe                                  226   Me        Me      2-NO.sub.2 -3,5-(Me).sub.2                             227   Et        Et      2-NO.sub.2 -3,5-(Me).sub.2                             228   Me        Me      2,3,5,6-F.sub.4                                        229   Et        Et      2,3,5,6-F.sub.4                                        230   Me        Me      2,3,4,5,6-F.sub.5                                      231   Et        Et      2,3,4,5,6-F.sub.5                                      232   Me        Me      2,3,4,5,6-Cl.sub.5                                     233   Et        Et      2,3,4,5,6-Cl.sub.5                                     234   Me        Me      2,3,4,5,6-(Me).sub.5                                   235   Et        Et      2,3,4,5,6-(Me).sub.5                                   __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                         Compound                                                                       No.          R.sup.1  R.sup.2   Y.sub.n                                        ______________________________________                                         236          Me       Me        H                                              237          Et       Et        H                                              238          Me       Me        4-Cl                                           239          Et       Et        4-Cl                                           240          Me       Me        2-Me                                           241          Et       Et        2-Me                                           242          Me       Me        2-OMe                                          243          Et       Et        2-OMe                                          244          Me       Me        4-CF.sub.3                                     245          Et       Et        4-CF.sub.3                                     246          Me       Me        2-OCH.sub.2 CF.sub.3                           247          Et       Et        2-OCH.sub.2 CF.sub.3                           248          Me       Me        2-COCH.sub.3                                   249          Et       Et        2-COCH.sub.3                                   250          Me       Me        2-CHO                                          251          Et       Et        2-CHO                                          252          Me       Me        2-COOMe                                        253          Et       Et        2-COOMe                                        254          Me       Me        2-NO.sub.2                                     255          Et       Et        2-NO.sub.2                                     256          Me       Me        4-NHCOCH.sub.3                                 257          Et       Et        4-NHCOCH.sub.3                                 ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                         Compound                                                                       No.          R.sup.1  R.sup.2   Y.sub.n                                        ______________________________________                                         258          Me       Me        H                                              259          Et       Et        H                                              260          Me       Me        1-Br                                           261          Et       Et        1-Br                                           262          Me       Me        1-Me                                           263          Et       Et        1-Me                                           264          Me       Me        1-OMe                                          265          Et       Et        1-OMe                                          266          Me       Me        1-CF.sub.3                                     267          Et       Et        1-CF.sub.3                                     268          Me       Me        1-OCH.sub.2 CF.sub.3                           269          Et       Et        1-OCH.sub.2 CF.sub.3                           270          Me       Me        1-COCH.sub.3                                   271          Et       Et        1-COCH.sub.3                                   272          Me       Me        1-CHO                                          273          Et       Et        1-CHO                                          274          Me       Me        3-COOMe                                        275          Et       Et        3-COOMe                                        276          Me       Me        1-NO.sub.2                                     277          Et       Et        1-NO.sub.2                                     278          Me       Me        3-NHCOCH.sub.3                                 279          Et       Et        3-NHCOCH.sub.3                                 ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                         Compound                                                                       No.         R.sup.1  R.sup.2   R.sup.3                                                                               R.sup.4                                  ______________________________________                                         280         Me       Me        H      H                                        281         Et       Et        H      H                                        282         Me       Me        Me     H                                        283         Et       Et        Me     H                                        284         Me       Me        Me     Me                                       285         Me       Et        Me     Me                                       286         Et       Et        Me     Me                                       287         Et       nPr       Me     Me                                       288         Et       iPr       Me     Me                                       289         nPr      nPr       Me     Me                                       ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                         Compound                                                                       No.         R.sup.1  R.sup.2   R.sup.3                                                                               R.sup.4                                  ______________________________________                                         290         Me       Me        H      H                                        291         Et       Et        H      H                                        292         Me       Me        Me     H                                        293         Et       Et        Me     H                                        294         Me       Me        Me     Me                                       295         Me       Et        Me     Me                                       296         Et       Et        Me     Me                                       297         Et       nPr       Me     Me                                       298         Et       iPr       Me     Me                                       299         nPr      nPr       Me     Me                                       ______________________________________                                    

                                      TABLE 6                                      __________________________________________________________________________     Compound                                                                       No.   R.sup.1   R.sup.2 X.sub.m                                                __________________________________________________________________________     301   Me        Me      H                                                      302   Me        Et      H                                                      303   Et        Et      H                                                      304   Et        nPr     H                                                      305   Et        iPr     H                                                      306   nPr       nPr     H                                                      307   CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 H                                                      308   CH(Me)-(CH.sub.2).sub.3 CH(Me)-                                                                  H                                                      309   CH(Et)-(CH.sub.2).sub.3 CH.sub.2                                                                 H                                                      310   Me        Me      2-Me                                                   311   Et        Et      2-Me                                                   312   Me        Me      3-Me                                                   313   Et        Et      3-Me                                                   314   Me        Me      4-Me                                                   315   Et        Et      4-Me                                                   316   CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 4-Me                                                   317   Me        Me      2-Et                                                   318   Et        Et      2-Et                                                   319   Me        Me      3-Et                                                   320   Et        Et      3-Et                                                   321   Me        Me      4-Et                                                   322   Et        Et      4-Et                                                   323   Me        Me      2-iPr                                                  324   Et        Et      2-iPr                                                  325   Me        Me      3-iPr                                                  326   Et        Et      3-iPr                                                  327   Me        Me      4-iPr                                                  328   Et        Et      4-iPr                                                  329   Me        Me      4-tBu                                                  330   Et        Et      4-tBu                                                  331   Me        Me      2-F                                                    332   Et        Et      2-F                                                    333   Me        Me      3-F                                                    334   Et        Et      3-F                                                    335   Me        Me      4-F                                                    336   Et        Et      4-F                                                    337   Me        Me      2-Cl                                                   338   Et        Et      2-Cl                                                   339   Me        Me      3-Cl                                                   340   Et        Et      3-Cl                                                   341   Me        Me      4-Cl                                                   342   Et        Et      4-Cl                                                   343   Me        Me      2-Br                                                   344   Et        Et      2-Br                                                   345   Me        Me      2-CH.sub.2 CHCH.sub.2                                  346   Et        Et      2-CH.sub.2 CHCH.sub.2                                  347   Me        Me      2-OMe                                                  348   Et        Et      2-OMe                                                  349   Me        Me      3-OMe                                                  350   Et        Et      3-OMe                                                  351   Me        Me      4-OMe                                                  352   Et        Et      4-OMe                                                  353   Me        Me      3-OEt                                                  354   Et        Et      3-OEt                                                  355   Me        Me      4-OEt                                                  356   Et        Et      4-OEt                                                  357   Me        Me      2-CF                                                   358   Et        Et      2-CF.sub.3                                             359   Me        Me      3-CF.sub.3                                             360   Et        Et      3-CF.sub.3                                             361   Me        Me      4-CF.sub.3                                             362   Et        Et      4-CF.sub.3                                             363   Me        Me      2-OCHF.sub.2                                           364   Et        Et      2-OCHF.sub.2                                           365   Me        Me      4-OCHF.sub.2                                           366   Et        Et      4-OCHF.sub.2                                           367   Me        Me      2-OCH.sub.2 CF.sub.3                                   368   Et        Et      2-OCH.sub.2 CF.sub.3                                   369   Me        Me      4-OCH.sub.2 CF.sub.3                                   370   Et        Et      4-OCH.sub.2 CF.sub.3                                   371   Me        Me      2-OCF.sub.2 CFClH                                      372   Et        Et      2-OCF.sub.2 CFClH                                      373   Me        Me      2-C.sub.6 H.sub.5                                      374   Et        Et      2-C.sub.6 H.sub. 5                                     375   Me        Me      2-CH.sub.2 C.sub.6 H.sub.5                             376   Et        Et      2-CH.sub.2 C.sub.6 H.sub.5                             377   Me        Me      2-OCH.sub.2 C.sub.6 H.sub.5                            378   Et        Et      2-OCH.sub.2 C.sub.6 H.sub.5                            379   Me        Me      2-COCH.sub.3                                           380   Et        Et      2-COCH.sub.3                                           381   Me        Me      2-COOMe                                                382   Et        Et      2-COOMe                                                383   Me        Me      4-COOMe                                                384   Et        Et      4-COOMe                                                385   Me        Me      2-CHO                                                  386   Et        Et      2-CHO                                                  387   Me        Me      2-NO.sub.2                                             388   Et        Et      2-NO.sub.2                                             389   Me        Me      4-NO.sub.2                                             390   Et        Et      4-NO.sub.2                                             391   Me        Me      2-CN                                                   392   Et        Et      2-CN                                                   393   Me        Me      3-CN                                                   394   Et        Et      3-CN                                                   395   Me        Me      4-CN                                                   396   Et        Et      4-CN                                                   397   Me        Me      2-NHCOCH.sub.3                                         398   Et        Et      2-NHCOCH.sub.3                                         399   Me        Me      4-NHCOCH.sub.3                                         400   Et        Et      4-NHCOCH.sub.3                                         401   Me        Me      2,6-(Me).sub.2                                         402   Me        Et      2,6-(Me).sub.2                                         403   Et        Et      2,6-(Me).sub.2                                         404   Et        nPr     2,6-(Me).sub.2                                         405   Et        iPr     2,6-(Me).sub.2                                         406   nPr       nPr     2,6-(Me).sub.2                                         407   CH(Me)-(CH.sub.2).sub.3 CH.sub.2                                                                 2,6-(Me).sub.2                                         408   Me        Me      2,4-(Me).sub.2                                         409   Et        Et      2,4-(Me).sub.2                                         410   Me        Me      3,4-(Me).sub.2                                         411   Et        Et      4-(Me).sub.2                                           412   Me        Me      3,5-(Me).sub.2                                         413   Et        Et      3,5-(Me).sub.2                                         414   Me        Me      2,3-(Me).sub.2                                         415   Et        Et      2,3-(Me).sub.2                                         416   Me        Me      2,6-(Et).sub.2                                         417   Et        Et      2,6-(Et).sub.2                                         418   Me        Me      2-Me-6-Et                                              419   Et        Et      2-Me-6-Et                                              420   Me        Me      2-Me-5-iPr                                             421   Et        Et      2-Me-5-iPr                                             422   Me        Me      2-iPr-5-Me                                             423   Et        Et      2-iPr-5-Me                                             424   Me        Me      2-Me-4-Cl                                              425   Et        Et      2-Me-4-Cl                                              426   Me        Me      2-Me-6-Cl                                              427   Et        Et      2-Me-6-Cl                                              428   Me        Me      3-Me-4-Cl                                              429   Et        Et      3-Me-4-Cl                                              430   Me        Me      2-Me-4-F                                               431   Et        Et      2-Me-4-F                                               432   Me        Me      2,4-F.sub.2                                            433   Et        Etr     2,4-F.sub.2                                            434   Me        Me      2,6-F.sub.2                                            435   Et        Et      2,6-F.sub.2                                            436   Me        Me      2,3-Cl.sub.2                                           437   Et        Et      2,3-Cl.sub.2                                           438   Me        Me      2,4-Cl.sub.2                                           439   Et        Et      2,4-Cl.sub.2                                           440   Me        Me      2,5-Cl.sub.2                                           441   Et        Et      2,5-Cl.sub.2                                           442   Me        Me      2,6-Cl.sub.2                                           443   Et        Et      2,6-Cl.sub.2                                           444   Me        Me      2-Cl-4-F                                               445   Et        Et      2-Cl-4-F                                               446   Me        Me      2-Cl-6-F                                               447   Et        Et      2-Cl-6-F                                               448   Me        Me      4-Cl-2-F                                               449   Et        Et      4-Cl-2-F                                               450   Me        Me      2-OMe-4-Me                                             451   Et        Et      2-OMe-4-Me                                             452   Me        Me      2,6-(OMe).sub.2                                        453   Et        Et      2,6-(OMe).sub.2                                        454   Me        Me      2-F-6-OMe                                              455   Et        Et      2-F-6-OMe                                              456   Me        Me      3-Cl-5-OMe                                             457   Et        Et      3-Cl-5-OMe                                             458   Me        Me      2-OMe-4-CHCHCH.sub.3                                   459   Et        Et      2-OMe-4-CHCHCH.sub.3                                   460   Me        Me      2-OMe-4-CH.sub.2 CHCH.sub.2                            461   Et        Et      2-OMe-4-CH.sub.2 CHCH.sub.2                            462   Me        Me      3,5-(CF.sub.3).sub.2                                   463   Et        Et      3,5-(CF.sub.3).sub.2                                   464   Me        Me      2-Cl-4-CF.sub.3                                        465   Et        Et      2-Cl-4-CF.sub.3                                        466   Me        Me      2-Cl-5-CF.sub.3                                        467   Et        Et      2-Cl-5-CF.sub.3                                        468   Me        Me      2-Me-6-COOMe                                           469   Et        Et      2-Me-6-COOMe                                           470   Me        Me      2-OMe-6-COOMe                                          471   Et        Et      2-OMe-6-COOMe                                          472   Me        Me      2-Cl-6-COOMe                                           473   Et        Et      2-Cl-6-COOMe                                           474   Me        Me      2-NO.sub.2 -3-Me                                       475   Et        Et      2-NO.sub.2 -3-Me                                       476   Me        Me      2-CN-4-F                                               477   Et        Et      2-CN-4-F                                               478   Me        Me      2-CN-4-Cl                                              479   Et        Et      2-CN-4-Cl                                              480   Me        Me      2-CN-4-Br                                              481   Et        Et      2-CN-4-Br                                              482   Me        Me      4-CN-2-F                                               483   Et        Et      4-CN-2-F                                               484   Me        Me      4-CN-2-Cl                                              485   Et        Et      4-CN-2-Cl                                              486   Me        Me      4-CN-2-Br                                              487   Et        Et      4-CN-2-Br                                              488   Me        Me      2,3,5-(Me).sub.3                                       489   Et        Et      2,3,5-(Me).sub.3                                       490   Me        Me      2,3,6-(Me).sub.3                                       491   Et        Et      2,3,6-(Me).sub.3                                       492   Me        Me      2,4,6-(Me).sub.3                                       493   Me        Et      2,4,6-(Me).sub.3                                       494   Et        Et      2,4,6-(Me).sub.3                                       495   Et        nPr     2,4,6-(Me).sub.3                                       496   Et        iPr     2,4,6-(Me).sub.3                                       497   nPr       nPr     2,4,6-(Me).sub.3                                       498   Me        Me      2,4-(Me).sub.2 -6-Cl                                   499   Et        Et      2,4-(Me).sub.2 -6-Cl                                   500   Me        Me      2,6-(Me).sub.2 -4-Cl                                   501   Et        Et      2,6-(Me).sub.2 -4-Cl                                   502   Me        Me      2,4-Cl.sub.2 -6-Me                                     503   Et        Et      2,4-Cl.sub.2 -6-Me                                     504   Me        Me      2,6-Cl.sub.2 -4-Me                                     505   Et        Et      2,6-Cl.sub.2 -4-Me                                     506   Me        Me      2,4-Cl.sub.2 -3-Me                                     507   Et        Et      2,4-Cl.sub.2 -3-Me                                     508   Me        Me      2,6-Cl.sub.2 -4-CF.sub.3                               509   Et        Et      2,6-Cl.sub.2 -4-CF.sub.3                               510   Me        Me      2,3,4-Cl.sub.3                                         511   Et        Et      2,3,4-Cl.sub.3                                         512   Me        Me      2,3,6-Cl.sub.3                                         513   Et        Et      2,3,6-Cl.sub.3                                         514   Me        Me      2,4,5-Cl.sub.3                                         515   Et        Et      2,4,5-Cl.sub.3                                         516   Me        Me      2,4,6-Cl.sub.3                                         517   Me        Et      2,4,6-Cl.sub.3                                         518   Et        Et      2,4,6-Cl.sub.3                                         519   Et        nPr     2,4,6-Cl.sub.3                                         520   Et        iPr     2,4,6-Cl.sub.3                                         521   nPr       nPr     2,4,6-Cl.sub.3                                         522   Me        Me      3,4,5-(OMe).sub.3                                      523   Et        Et      3,4,5-(OMe).sub.3                                      524   Me        Me      2,4-Cl.sub.2 -6-COOMe                                  525   Et        Et      2,4-Cl.sub.2 -6-COOMe                                  526   Me        Me      2-NO.sub.2 -3,5-(Me).sub.2                             527   Et        Et      2-NO.sub.2 -3,5-(Me).sub.2                             528   Me        Me      2,3,5,6-F.sub.4                                        529   Et        Et      2,3,5,6-F.sub.4                                        530   Me        Me      2,3,4,5,6-F.sub.5                                      531   Et        Et      2,3,4,5,6-F.sub.5                                      532   Me        Me      2,3,4,5,6-Cl.sub.5                                     533   Et        Et      2,3,4,5,6-Cl.sub.5                                     534   Me        Me      2,3,4,5,6-(Me).sub.5                                   535   Et        Et      2,3,4,5,6-(Me).sub.5                                   __________________________________________________________________________

                  TABLE 7                                                          ______________________________________                                         Compound                                                                       No.          R.sup.1  R.sup.2   Y.sub.n                                        ______________________________________                                         536          Me       Me        H                                              537          Et       Et        H                                              538          Me       Me        4-Cl                                           539          Et       Et        4-Cl                                           540          Me       Me        2-Me                                           541          Et       Et        2-Me                                           542          Me       Me        2-OMe                                          543          Et       Et        2-OMe                                          544          Me       Me        4-CF.sub.3                                     545          Et       Et        4-CF.sub.3                                     546          Me       Me        2-OCH.sub.2 CF.sub.3                           547          Et       Et        2-OCH.sub.2 CF.sub.3                           548          Me       Me        2-COCH.sub.3                                   549          Et       Et        2-COCH.sub.3                                   550          Me       Me        2-CHO                                          551          Et       Et        2-CHO                                          552          Me       Me        2-COOMe                                        553          Et       Et        2-COOMe                                        554          Me       Me        2-NO.sub.2                                     555          Et       Et        2-NO.sub.2                                     556          Me       Me        4-NHCOCH.sub.3                                 557          Et       Et        4-NHCOCH.sub.3                                 ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                         Compound                                                                       No.          R.sup.1  R.sup.2   Y.sub.n                                        ______________________________________                                         558          Me       Me        H                                              559          Et       Et        H                                              560          Me       Me        1-Br                                           561          Et       Et        1-Br                                           562          Me       Me        1-Me                                           563          Et       Et        1-Me                                           564          Me       Me        1-OMe                                          565          Et       Et        1-OMe                                          566          Me       Me        1-CF.sub.3                                     567          Et       Et        1-CF.sub.3                                     568          Me       Me        1-OCH.sub.2 CF.sub.3                           569          Et       Et        1-OCH.sub.2 CF.sub.3                           570          Me       Me        1-COCH.sub.3                                   571          Et       Et        1-COCH.sub.3                                   572          Me       Me        1-CHO                                          573          Et       Et        1-CHO                                          574          Me       Me        3-COOMe                                        575          Et       Et        3-COOMe                                        576          Me       Me        1-NO.sub.2                                     577          Et       Et        1-NO.sub.2                                     578          Me       Me        3-NHCOCH.sub.3                                 579          Et       Et        3-NHCOCH.sub.3                                 ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         Compound                                                                       No.         R.sup.1  R.sup.2   R.sup.3                                                                               R.sup.4                                  ______________________________________                                         580         Me       Me        H      H                                        581         Et       Et        H      H                                        582         Me       Me        Me     H                                        583         Et       Et        Me     H                                        584         Me       Me        Me     Me                                       585         Me       Et        Me     Me                                       586         Et       Et        Me     Me                                       587         Et       nPr       Me     Me                                       588         Et       iPr       Me     Me                                       589         nPr      nPr       Me     Me                                       ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         Compound                                                                       No.         R.sup.1  R.sup.2   R.sup.3                                                                               R.sup.4                                  ______________________________________                                         590         Me       Me        H      H                                        591         Et       Et        H      H                                        592         Me       Me        Me     H                                        593         Et       Et        Me     H                                        594         Me       Me        Me     Me                                       595         Me       Et        Me     Me                                       596         Et       Et        Me     Me                                       597         Et       nPr       Me     Me                                       598         Et       iPr       Me     Me                                       599         nPr      nPr       Me     Me                                       ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                         Compounds                                                                      No.          R.sup.1   R.sup.2   X.sub.p                                       ______________________________________                                         600          Me        Me        3-CF.sub.3                                    601          Et        Et        3-CF.sub.3                                    602          Me        Me        4-CF.sub.3                                    603          Et        Et        4-CF.sub.3                                    604          Me        Me        5-CF.sub.3                                    605          Et        Et        5-CF.sub.3                                    606          Me        Me        6-CF.sub.3                                    607          Et        Et        6-CF.sub.3                                    608          Me        Me        3-Cl-4-CF.sub.3                               609          Et        Et        3-Cl-4-CF.sub.3                               610          Me        Me        3-Cl-5-CF.sub.3                               611          Et        Et        3-Cl-5-CF.sub.3                               612          Me        Me        3-Cl-6-CF.sub.3                               613          Et        Et        3-Cl-6-CF.sub.3                               ______________________________________                                    

A method of manufacturing the compound according to the present invention and expressed by general formula (I) will now be described. However, the compounds according to the present invention is not limited to those manufactured by the following methods. ##STR15## in which Z is a halogen atom, and A, l, R¹ and R² are the same as in general formula (I).

The compounds according to the present invention and expressed by general formula (I) can be obtained by causing a triazole derivatives expressed by general formula (II) and sulfamoylhalide expressed by general formula (III) to react with each other, preferably in a solvent, in the presence of a base. Although the quantities of the materials are not particularly limited, it is preferable that sulfamoylhalide (III) be 1 to 1.5 equivalents and the base be 1 to 5 equivalents with respect to 1 equivalent of triazole derivative (II).

The reaction temperature may be arbitrarily determined so far as it ranges from the temperature realized by ice cooling to the boiling point of the solvent.

Although the reaction time varies depending upon the conditions, the reactions can usually be completed in 10 minutes to 24 hours.

The solvent may be any one of the following materials selected from the group consisting of aliphatic hydrocarbons such as hexane, heptane, ligroin or petroleum ether; aromatic hydrocarbons such as benzene, toluene or xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene or dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone or cyclohexanone; nitro compounds such as nitroethane or nitrobenzene; nitriles such as acetonitrile or isobutylonitrile; tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributylamine or N-methylmorpholine; acid amides such as N,N-dimethylformamide; and sulfur compounds such as dimethyl sulfoxide or sulforan; and their mixtures.

Examples of a base include organic bases such as pyridine, triethylamine or N,N-dietylaniline; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or sodium hydride; and alkali metal alkoxides such as sodium methoxide or sodium ethoxide.

Water is added to the solution, in which the reactions have been allowed to take place, and then subjected to normal post-processes such as extraction of the organic solvent, immersion, and the like. If necessary, the products may be purified by recrystallization, silica gel column chromatography or medium-pressure liquid chromatography.

The triazole derivatives expressed by general formula (II) can be manufactured by the following method (1) or (2). However, the triazole derivatives are not limited to that manufactured by the following methods.

(1) If l of the foregoing general formula is 1, ##STR16## in which Z is a halogen atom and A is the same as in general formula (I).

The compounds expressed by general formula (II-1) can be obtained by causing the compounds expressed by general formula (IV) and the compounds expressed by general formula (V) to react with each other in an adequate solvent in the presence of a basic substance. Although the quantities of the materials are not particularly limited, the compound (V) Is preferably 1 to 1.2 equivalents with respect to 1 equivalent of the compound (IV).

The reaction temperature may be arbitrarily determined so far as it ranges from a level realized by ice-cooling to the boiling point of the solvent.

Although the reaction time varies depending upon the conditions, the reactions can usually be completed in 1 hour to 24 hours.

The solvent may be any of the following materials selected from a group consisting of aliphatic hydrocarbons such as hexane, heptane, ligroin or petroleum ether; aromatic hydrocarbons such as benzene, toluene or xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene or dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methylisobutyl ketone, isophorone or cyclohexanone; nitro compounds such as nitroethane or nitrobenzene; nitriles such as acetonitrile or isobutylonitrile; tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributyl amine or N-methylmorpholine; acid amides such as N,N-dimethylformamide; and sulfur compounds such as dimethyl sulfoxide or sulforan; and their mixtures.

Examples of a base include organic bases such as pyridine, triethylamine or N,N-dietylanitine; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or sodium hydride; and alkali metal alkoxides such as sodium methoxide or sodium ethoxide.

The products (II-1) can be isolated from the mixture of reactants by a usual method and can easily be purified by recrystallization or column chromatography.

(2) If l of the foregoing general formula is 0, the triazole derivatives expressed by general formula (II-2) can be manufactured by the following method A or B. ##STR17## in which A is the same as in general formula (I).

The compounds expressed by general formula (VII) can be obtained by causing the compounds expressed by general formula (VI) and 3-mercapto-1,2,4-triazole to react with each other in an adequate solvent in the presence of a basic substance. Although the quantities of the materials are not particularly limited, 3-mercapto-1,2,4-triazole Is preferably 1 to 1.2 equivalents with respect to 1 equivalent of the compound (VI).

The reaction temperature may be arbitrarily determined so far as it ranges from -20° C. to 100° C.

Although the reaction time varies depending upon the conditions, the reactions can usually be completed in 1 hour to 24 hours.

The basic material may be an inorganic material such as alkaline carbonate or caustic alkali. Although the quantity of the basic material is not particularly limited, the basic material is preferably 1 to 1.5 equivalents with respect to 1 equivalent of the compound (VI).

The products (VII) can be isolated from the mixture of reactants by a usual method and can easily be purified by recrystallization or column chromatography.

The compounds expressed by general formula (II-2) can be obtained by causing the compounds expressed by general formula (VII) to react in an adequate solvent in the presence of an oxidant. Although the quantities of the materials are not particularly limited, the oxidant is preferably 2 to 5 equivalent with respect to 1 equivalent of the compound (VII).

The reaction temperature may be arbitrarily determined so far as it ranges from room temperature to 100° C. Although the reaction time varies depending upon the conditions, the reactions can usually be completed in 30 minutes to 24 hours.

Examples of solvent include: ketones such as acetone; ethers such as tetrahydrofuran, dioxane and diethyl ether; esters such as ethyl acetate; halogenated hydrocarbons such as dichloromethane; aromatic hydrocarbons such as chlorobenzene; or polar solvents such as N,N-dimethylformamide or acetic acid or their mixtures. Further, a mixture system of water and the foregoing solvent may be employed.

Although the quantity of the solvent is not particularly limited, normally the solvent is 5 to 20 times, by wt %, that of the compound (VII) is appropriate.

Examples of oxidant include aromatic peracids such as methachloroperbenzoic acid; aliphatic peracids such as acetyl hydroperoxide; or pertrifluoroacetate and hydrogen peroxide.

The products (II-2) can be isolated from the mixture of reactants by a usual method and can easily be purified by recrystallization or column chromatography. ##STR18## in which W is a halogen atom and A is the same as in general formula (I).

The compounds expressed by general formula (VII) can be obtained by causing the compounds expressed by general formula (VIII) and 3-mercapto-1,2,4-triazole to react with each other in an adequate solvent in the presence of a basic substance. Although the quantities of the materials are not particularly limited, 3-mercapto-1,2,4-triazole is preferably 1 to 1.2 equivalents with respect to 1 equivalent of the compound (VIII).

The reaction temperature may be arbitrarily determined so far as It ranges from a level realized by ice-cooling to the boiling point of the solvent. Although the reaction time varies depending upon the conditions, the reactions can usually be completed in 1 hour to 24 hours.

Examples of solvent may include: ketones such as acetone; ethers such as tetrahydrofuran, dioxane and diethyl ether; esters such as ethyl acetate; halogenated hydrocarbons such as dichloromethane; aromatic hydrocarbons such as chlorobenzene; or polar solvents such as N,N-dimethylformamide or acetic acid or their mixtures. Although the quantity of the solvent is not particularly limited, the quantity of the solvent is preferably 1.05 to 20 times, by wt %, the quantity of the compound (VIII).

Examples of basic materials include: inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or sodium hydride; organic bases such as pyridine, triethylamine or N,N-diethyl aniline; and alkali metal alkoxides such as sodium methoxide or sodium ethoxide.

The products (VII) can be isolated from the mixture of reactants by a usual method and can easily be purified by recrystallization or column chromatography.

The compounds expressed by general formula (II-2) can be manufactured from the compounds expressed by general formula (VII) by a method similar to method A.

[II] FUNGICIDE

The fungicidal compositions according to the present invention contains a sulfamoyltriazole derivative expressed by general formula (I) as an effective component thereof.

When the compounds expressed by general formula (I) is used as the fungicide, they are mixed with a carrier, a diluent or an additive and an adjuvant by a known method while being formed into a formulation which is usually employed as agricultural chemicals, for example, powder material, granules, water-dispersible powder, emulsion, water soluble powder or flowable material. The compound may be mixed or used together with other agricultural chemicals, for example, fungicities, insecticides, miticides, herbicides, plant growth regulators, fertilizers and soil conditioners.

In particular, the mixed use with other fungicides can reduce the dosage of the compound, and therefore save labor. Further, the cooperative operation of the chemicals enlarges the fungicidal spectrum. In addition, the synergetic operation enables an ever greater effect to be obtained.

The carrier and the diluent may be normal solid or liquid carriers.

The solid carrier is exemplified by clay represented by the kaolinite group, montmorillonite group, illite group and polygorskite group. Specifically, it is exemplified by inorganic substances such as pyrophillite, attapulgite, sepeorite, kaolinite, bentonite, vermiculite, mica or talc; other inorganic substances such as gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, silicic anhydride or synthetic calcium silicate; vegetable organic substances such as soybean meal, tobacco flour, walnut flour, wheat flour, wood flour, starch or crystalline cellulose; synthetic or natural polymers such as coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, covar gum or dam mar gum; waxes such as carnauba wax or beeswax; and urea.

Examples of adequate liquid carriers include pararline- or naphthene-hydrocarbons such as kerosene, mineral oil, spindle oil or white oil: aromatic hydrocarbons such as xylene, ethyl benzene, cumene or methyl naphthalene; chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene or ortho chlorotoluene; ethers such as dioxane or tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone or isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate or diethyl succinate; alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol or benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether or diethylene glycol butyl ether; polar solvents such as dimethyl formamide or dimethyl sulfoxide; and water.

Further, a surface active agent and another adjuvant may be added to emulsificate, disperse, wet, spread, develop, bond, regulate degradation, stabilize the effective components, improve the fluidity, prevent corrosion and prevent freezing.

The surface active agent may be a nonionic compound, an anion compound, a cation compound or a dipolar compound. A nonionic and/or cation compound is usually employed.

Appropriate nonionic surface active agents include; compounds prepared by polymerizing and adding ethylene oxide to a higher alcohol, such as lauryl alcohol, stearyl alcohol or oleyl alcohol: compounds prepared by polymerizing and adding ethylene oxide to alkyl naphthol such as butyl naphthol or octyl naphthol; compounds prepared by polymerizing and adding ethylene oxide to a higher fatty acid such as palmitic acid, stearic acid or oleic acid; higher fatty acid esters of a polyatomic alcohol such as sorbitan; compounds prepared by polymerizing and adding ethylene oxide to the foregoing higher fatty acid ester; and compounds prepared by block-polymerizing ethylene oxide and propylene oxide.

The preferred cation surface active agents include: alkyl sulfonic ester salts such as sodium lauryl sulfate or oleyl alcohol sulfuric ester amine salt; alkyl sulfonates such as sulfone succinate dioctyl sodium ester or 2-ethyl hexene sodium sulfonate; and aryl sulfonates such as isopropyl naphthalene sodium sulfonate, methylene bisnapthalene sodium sulfonate, lignosulfonic sodium or dodecylbenzene sodium sulfonate.

In order to improve the characteristics of the fungicide and to enhance the effect thereof, polymers or other adjuvants such as casein, gelatin, albumin, glue, alginic soda, carboxylic methyl cellulose, methyl cellulose, hydroxyethyl cellulose or polyvinyl alcohol may be used.

The foregoing carriers and the various adjuvants may be arbitrarily used alone or in the form of a mixture to meet the desired object considering the system of formulation and the specific use.

Although the content of the compound according to the present invention in each of the foregoing prepared chemicals as an effective compound varies depending upon the formulation of the prepared chemicals, the preferred content is usually 0.1 wt % to 99 wt %, more preferably 1 wt % to 80 wt %.

In a water-dispersible powder according to the present invention, the compound serving as an effective component usually comprises 5% to 90% of the mixture with the solid carrier and dispersed wetting agent as a balance. If necessary, a protection colloid agent, an antifoaming agent and the like may be added.

In granule form according to the invention, the compound serving as an effective component usually comprises, for example, 1 wt % to 35 wt % of the mixture with the solid carrier and surface active agent as a balance. The compound serving as the effective component is uniformly mixed with the solid carrier or uniformly secured to or adsorbed in the surface of the solid carrier. The grain size is about 0.2 mm to 1.5 mm.

In an emulsion according to the invention, the compound serving as an effective component usually comprises, for example, 5 wt % to 30 wt % of the mixture with the emulsifier comprise about 5 wt % to 20 wt % and the balance composed of a liquid carrier. If necessary, a spreading agent and rust preventives may be added.

In a flowable material according to the invention, the compound serving as an effective component usually comprises, for example, 5 wt % to 50 wt % of the mixture with the disperse wetting agent comprise 3 wt % to 10 wt % and the balance composed of water. If necessary a protective collide agent, rust preventives and antifoaming agent may be added.

The sulfamoyltriazole derivative according to the present invention can be used as a fungicide in the form of the compound expressed by general formula (I) or in the form of any one of the foregoing formulations.

Although the concentration of the compound according to the present invention cannot be generalized because it varies depending upon the kind of plants to be used on, the application method, the formulation, and the application rate, the compound expressed by general formula (I) may be added by 0.1 ppm to 10,000 ppm to serve as the effective component when the compound is used in foliage treatment, preferably 1 ppm to 500 ppm. In soil treatment use, it may be contained by 10 g/ha to 100,000 g/ha, preferably 200 g/ha to 20,000 g/ha.

[EXAMPLES]

The present invention will now be described by providing examples.

(1) Synthesis of Precursor Reference Example 1

Preparation of 3-(2,4,6-trimethylphenoxysulfonyl)-1,2,4-triazole

4.1 g of 2,4,6-trimethylphenol was dissolved in 15 ml of dichloromethane, and 4.2 ml of triethylamine was added while stirring the solution. Further, 4.6 g of 3-chlorosulfonyl-1,2,4-triazole was gradually added while being cooled with ice and stirred. Then, the solution was stirred at room temperature for 14 hours. After that, 2N hydrochloric acid was added to separate the components. The organic layer was washed with water, and then it was dried with magnesium sulfate. Then, the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 3.0 g of the titled compound was obtained.

Reference Example 2

Preparation of 3-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl-oxysulfonyl)-1,2,4-triazole

5.4 g of 3,3-dimethyl-5-hydroxy-2,3-dihydrobenzofuran was dissolved in 30 ml of tetrahydrofuran, and then 4.6 ml of triethylamine was added while stirring the solution. Then, 5.0 g of 3-chlorosulfonyl-1,2,4-triazole was gradually added while cooling with ice and stirring the solution. Then, this was stirred for 14 hours. Tetrahydrofuran was evaporated, and 2N hydrochloric acid was added and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate, and the solvent was removed, so that coarse crystals were obtained. This was then recrystallized from n-hexane/ethyl acetate, so that 2.7 g of the titled compound was obtained.

Reference Example 3

Preparation of 3-(2,4-dichloro-3-methylphenoxysulfonyl)-1,2,4-triazole

2.33 g of 2.4-dichloro-3-methylphenol was dissolved in 15 ml of tetrahydrofuran, and 1.84 ml of triethylamine was added while stirring the solution. Then, 2.0 g of 3-chlorosulfonyl-1,2,4-triazole was gradually added while cooling with ice and stirring the solution. Then, the solution was stirred at room temperature for 14 hours. Tetrahydrofuran was removed by distillation at reduced pressure, 2N hydrochloric acid was added, and extracted with ethyl acetate. The organic layer was washed with brine, and dried with magnesium sulfate. Then, the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 2.25 g of the titled compound was obtained.

Reference Example 4

Preparation of 3-[4-(trifluoromethyl)phenylthiol-1,2,4-triazole

(A) 62.4 ml of concentrated hydrochloric acid was dissolved in 45 ml of water, and 60 g of p-aminobenzotrifluoride was added. Then, 28.2 g of sodium nitrite dissolved in 60 ml of water was slowly dropped in at 5° C., and the solution was stirred for 30 minutes.

(B) 25.1 g of potassium hydroxide was dissolved in 100 ml of water, and 41.4 g of 3-mercapto-1,2,4-triazole was added.

The solution obtained in the process (B) was heated to 55° C., and the solution obtained in the process (A) was gradually added. Then, the resulting solution was stirred for 40 minutes. Chloroform was added to the reactant solution, and this was stirred for 20 minutes. Then, impurities were removed by filtration, and the chloroform layer was washed with water and brine. The organic layer was dried with magnesium sulfate, evaporated and a residue was purified by silica gel column chromatography. As a result, 47.2 g (yield was 52%) of the titled compound was obtained.

Reference Example 5

Preparation of 3-(4-nitrophenylthio)-1,2,4-triazole

5 g of 3-mercapto-1,2,4-triazole was dissolved in 40 ml of N,N-dimethylformamide, and 2.17 g of sodium hydride (60% in mineral oil) was added at 0° C.. The solution was stirred at the same temperature for one hour, and then 7.78 g of 1-chloro-4-nitrobenzene was added. The solution was stirred at room temperature for one hour, and refluxed for 2 hours. Then, 10% hydrochloric acid was added to the reactant solution, it was extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate, and the solvent was evaporated, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 7.72 g of the titled compound was obtained (at a yield of 66%).

Reference Example 6

Preparation of 3-[4-(trifluoromethyl)phenylsulfonyl]-1,2,4-triazole

76.4 g of 3-[4-(trifluoromethyl)phenylthio]-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 4 was dissolved in 400 ml of acetic acid, and 140 g of 30% hydrogen peroxide solution was added. Then, the temperature was gradually raised, and the solution was stirred at 100° C. for three hours. Then, the reactant solution was cooled to room temperature, and a water solution of sodium thiosulfate was added. Then, precipitate was filtered, so that 66.4 g of the titled compound was obtained (at a yield of 77%).

(2) Preparation of Sulfamoyl Triazole Derivative Example 1

Preparation of 1-dimethylsulfamoyl-3-(3-trifluoromethylphenoxysulfonyl)-1,2,4-triazole (Compound No. 59)

1.0 g of 3-(3-trifluoromethylphenoxysulfonyl)-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 1 was dissolved in 10 ml of acetonitrile. Then, 0.57 g of potassium carbonate was added, and 0.59 g of dimethylsulfamoylchloride was gradually added at room temperature while stirring them. Then, they were refluxed for one hour, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate, and then the solvent was removed by distillation and the residue was purified by silica gel chromatography. As a result, 1.33 g of the titled compound was obtained.

Example 2

Preparation of 1-dimethylsulfamoyl-3-(4-trifluoromethylphenoxysulfonyl)-1,2,4-triazole (Compound No. 61).

1.0 g of 3-(4-trifluoromethylphenoxysulfonyl)-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 3 was dissolved in 10 ml of acetonitrile. Then, 0.57 g of potassium carbonate anhydride was added, and 0.59 g of dimethylsulfamoyl chloride was gradually added at room temperature while stirring the solution. The solution was then refluxed for one hour, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate, and then the solvent was removed by distillation and the residue was purified by silica gel chromatography. As a result, 1.18 g of the titled compound was obtained.

Example 3

Preparation of 1-dimethylsulfamoyl-3-(4-chloro-2-methylphenoxysulfonyl)-1,2,4-triazole (Compound No. 124)

0.57 g of 3-(4-chloro-2-methylphenoxysulfonyl)-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 1 was dissolved in 10 ml of acetonitrile, and 0.35 g of potassium carbonate was added, and 0.36 g of dimethylsulfamoylchloride was gradually added at room temperature while stirring the solution. The solution was then refluxed for one hour, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate. The solvent was removed by distillation, so that coarse crystals were obtained. This was recrystallized from n-hexane/ethyl acetate, so that 0.65 g of the titled compound was obtained.

Example 4

Preparation of 1-dimethylsulfamoyl-3-(2,4,6-trimethylphenoxysulfonyl)-1,2,4-triazole (Compound No. 192)

24.2 g of 3-(2,4,6-trimethylphenoxysulfonyl)-1,2,4-triazole was dissolved in 200 ml of acetonitrile, and 15.0 g of potassium carbonate was added, and 15.6 g of dimethylsulfamoylchloride was gradually added at room temperature while being stirred. Then, the solution was refluxed for one hour, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate. Then, the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 30.94 g of the titled compound was obtained.

Example 5

Preparation of 1-dimethylsulfamoyl-3-(2,4,-dichloro-3-methylphenoxysulfonyl)-1,2,4-triazole (Compound No. 206)

1.0 g of 3-(2,4-dichloro-3-methylphenoxysulfonyl)-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 3 was dissolved in 15 ml of acetonitrile. Then, 0.54 g of potassium carbonate was added, and 0.56 g of dimethylsulfamoylchloride was gradually added at room temperature while being stirred. The solution was then refluxed for one hour, and the reactant solution was added and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate. Then, the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 1.05 g of the titled compound was obtained.

Example 6

Preparation of 1-dimethylsulfamoyl-3-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl-oxysulfonyl)-1,2,4-triazole (Compound No. 294)

1.00 g of 3-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl-oxysulfonyl)-1,2,4-triazole synthesized by a method similar to that employed to prepare the precursor according to Reference Example 2 was dissolved in 10 ml of acetonitrile. Then, 0.56 g of potassium carbonate was added, and 0.58 g of dimethylsulfamoylchloride was gradually added at room temperature while being stirred. The solution was then refluxed for one hour, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate, and then the solvent was removed by distillation, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 1.13 g of the titled compound was obtained.

Example 7

Preparation of 1-dimethylsulfamoyl-3-[4-(trifluoromethyl)phenylsulfonyl]-1,2,4-triazole (Compound No. 361)

66.4 g of 3-[4-(trifluoromethyl)phenylsulfonyl]-1,2,4-triazole synthesized by a method similar to that for preparing the precursor according to the Reference Example 6 was dissolved in 500 ml of acetonitrile. Then, 75.0 g of potassium carbonate was added, and 50.6 g of dimethylsulfamoylchloride was gradually added at room temperature while being stirred. The solution was then refluxed for two hours, and the reactant solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried with magnesium sulfate, and then the solvent was evaporated, so that coarse crystals were obtained. The coarse crystals were recrystallized from n-hexane/ethyl acetate, so that 42.7 g of the titled compound was obtained (the yield was 47%).

The ¹ H-NMR peak values and the melting points of the substances according to the Examples and Reference Examples are shown in Table 12.

                  TABLE 12                                                         ______________________________________                                         Compound                      Melting                                          No.     NMR δ (ppm) Solvent CDCl.sub.3                                                                 point (°C.)                               ______________________________________                                          1      2.99(s, 6H), 7.1˜7.4(m, 3H)                                                                    117.0˜118.4                                 23     1.18(s, 3H), 1.20(s, 3H), 3.05(s, 6H)                                                                77.4˜80.6                                          3.32(sep, 1H), 7.1˜7.4(m, 4H), 8.71(s,                                   1H)                                                                     37     3.05(s, 6H), 7.2˜7.6(m, 4H), 8.69(s,                                                           117.8˜119.6                                        1H)                                                                     39     3.03(s, 6H), 7.1˜7.4(m, 4H), 8.65(s,                                                           101.1˜102.9                                        1H), 8.01(d, 2H), 8.75(s, 1H)                                           41     3.03(s, 6H), 7.1˜7.5(m, 4H), 8.63(s,                                                           139.6˜141.6                                        1H)                                                                     47     3.02(s, 6H), 3.67(s, 3H), 6.7˜7.5(m,                                                           148.5˜151.0                                        4H), 8.77(s, 1H)                                                        49     2.99(s, 6H), 3.74(s, 3H), 6.6˜7.1(m,                                                           74.5˜76.1                                          4H), 8.59(s, 1H)                                                        59     3.01(s, 6H), 7.3˜7.6(m, 4H), 8.59(s,                                                           Oil                                                      1H)                                                                     61     3.01(s, 6H), 7.38, 7.61(ABq, 1H), 8.63                                                               125.8˜127.5                                        (s, 1H)                                                                 81     3.04(s, 6H), 3.85(s, 3H), 7.26˜7.96(m,                                                         131.3˜132.8                                        4H), 8.67(s, 1H)                                                        83     3.00(s, 66H), 3.87(s, 3H), 7.27, 7.99                                                                127.7˜130.0                                        (ABq, 4H), 8.60(s, 1H)                                                  89     3.06(s, 6H), 7.47, 8.20(ABq, 4H), 8.63                                                               139.4˜141.7                                        (s, 1H)                                                                 91     3.11(s, 6H), 7.44˜7.79(m, 4H), 8.63(s,                                                         135.2˜137.6                                        1H)                                                                     93     3.08(s, 6H), 7.50˜7.68(m, 4H), 8.72(s,                                                         136.9˜139.6                                        1H)                                                                     95     3.07(s, 6H), 7.43, 7.72(ABq, 4H), 8.70                                                               184.9˜188.3                                        (s, 1H)                                                                101     2.25(s, 6H), 3.05(s, 6H), 7.03(s, 3H),                                                               100.1˜101.4                                        8.63(s, 1H)                                                            124     2.23(s, 3H), 3.00(s, 6H), 7.12(s, 2H)                                                                96.0˜97.3                                          8.55(s, 1H)                                                            136     3.02(s, 6H), 7.1˜7.6(m, 3H), 8.63(s,                                                           116.7˜119.3                                        1H)                                                                    140     3.06(s, 6H), 7.2˜7.6(m, 3H), 8.65(s,                                                           128.5˜130.8                                        1H)                                                                    152     3.03(s, 6H), 3.67(s, 6H), 6.3˜7.2(m,                                                           156.2˜159.5                                        3H), 8.61(s, 1H)                                                       164     3.07(s, 6H), 7.5˜7.8(m, 3H), 8.71(s,                                                           109.3˜110.8                                        1H)                                                                    166     3.08(s, 6H), 7.5˜7.65(m, 2H), 7.80(s,                                                          117.6˜120.0                                        1H), 8.72(s, 1H)                                                       192     2.22(s, 6H), 2.26(s, 3H), 3.08(s, 6H),                                                               113.4˜115.7                                        6.86(bs, 2H), 8.68(s, 1H)                                              198     2.24(s, 3H), 2.34(s, 3H), 3.04(s, 6H),                                                               131.5˜133.5                                        8.59(s, 1H)                                                            206     2.44(s, 3H), 3.05(s, 6H), 7.28(s, 2H),                                                               149.2˜151.6                                        8.63(s, 1H)                                                            210     3.06(s, 6H), 7.42(s, 2H), 8.66(s, 1H)                                                                153.6˜156.4                                212     3.06(s, 6H), 7.28(s, 2H), 8.64(s, 1H)                                                                140.5˜142.8                                216     3.03(s, 6H), 7.33(s, 2H), 8.62(s, 1H)                                                                149.3˜151.2                                284     1.34(s, 6H), 3.00(s, 2H), 3.03(s, 6H),                                                               136.7˜138.7                                        6.5˜7.2(m, 3H), 8.59(s, 1H)                                      294     1.27(s, 6H), 3.00(s, 6H), 4.19(s, 2H),                                                               108.4˜111.0                                        6.5˜7.2(m, 3H), 8.58(s, 1H)                                      301     3.05(s, 6H), 7.55˜7.75(m, 3H),                                                                 126.1˜128.5                                        8.09˜8.17(m, 2H), 8.58(s, 1H)                                    310     2.68(s, 3H), 3.07(s, 6H), 7.34(d, 1H),                                                               113.6˜114.0                                        7.44(t, 1H), 7.58(dt, 1H), 8.25(dd, 1H),                                       8.60(s, 1H)                                                            312     2.45(s, 3H), 3.05(s, 6H), 7.42˜7.55(m,                                                         102.1˜102.4                                        2H), 7.88˜7.98(m, 2H), 8.58(s, 1H)                               314     2.46(s, 3H),3.06(s, 6H), 7.39(d, 2H),                                                                137.6˜139.6                                        7.88˜7.98(m, 2H), 8.58(s, 1H)                                    337     3.04(s, 6H), 7.48˜7.70(m, 3H), 8.38                                                            133.0˜134.8                                        (dd, 1H), 8.62(s, 1H)                                                  339     3.07(s, 6H), 7.54(t, 1H), 7.61˜7.70(m,                                   1H), 7.97˜8.06(m, 1H), 8.07˜8.15                                   (m, 1H), 8.61(s, 1H)                                                   341     3.05(s, 6H), 7.57(d, 2H), 8.06(d, 2H),                                                               122.5˜124.2                                        8.60(s, 1H)                                                            357     3.03(s, 6H), 7.82˜7.97(m, 3H),                                                                 122.8˜124.9                                        8.55˜8.64(m, 1H), 8.56(s, 1H)                                    359     3.07(s, 6H), 7.77(t, 1H), 7.96(d, 1H),                                                               122.5˜123.7                                        8.34(d, 1H), 8.40(s, 1H), 8.61(s, 1H)                                  361     3.07(s, 6H), 7.87(d, 2H), 8.28(d, 2H),                                                               153.6˜155.6                                        8.61(s, 1H)                                                            363     3.04(s, 6H), 6.50(t, 1H), 7.13˜7.90(m,                                                         105.8˜108.0                                        3H), 8.25(dd, 1H), 8.56(s, 1H)                                         389     2.95(s, 6H), 8.31(d, 2H), 8.48(d, 2H),                                                               189.5˜192.0                                        9.46(s, 1H) Solvent DMSO                                               492     2.28(s, 3H), 2.68(s, 6H), 3.02(s, 6H),                                                               181.0˜185.7                                        6.90(s, 2H), 8.47(s, 1H)                                               506     2.51(s, 3H), 3.05(s, 6H), 7.50(d, 1H),                                                               148.0˜152.5                                        8.11(d, 1H), 8.53(s, 1H)                                               540     3.06(s, 6H), 8.07˜8.53(m, 2H), 8.55(s,                                                         139.4˜142.7                                        1H), 8.88(bs, 1H)                                                      610     3.05(s, 6H), 8.09(bs, 1H), 8.57(bs, 1H),                                                             137.5˜139.5                                        8.61(s, 1H)                                                            ______________________________________                                    

Formulation examples of chemicals using the compounds according to the present invention will now be described. The "parts" used below means parts by weight.

Example Chemical 1 (Emulsion)

    ______________________________________                                         Compound No. 192        10                                                     Xylene                  45                                                     Dodecylbenzenesulfonic acid calcium                                                                     7                                                     Polyoxy ethylene styrylphenyl ether                                                                    13                                                     dimethylformamide       25                                                     ______________________________________                                    

The foregoing materials were uniformly mixed and dissolved, so that 100 parts of emulsion were obtained.

Example Chemical 2 (Water-Dispersible-Powder)

    ______________________________________                                         Compound No. 361          20                                                   Diatomaceous earth        70                                                   Lignosulfonic acid calcium                                                                                5                                                   Naphthalenesulfonic acid formalin condensate                                                              5                                                   ______________________________________                                    

The foregoing materials were mixed and crushed, so that 100 parts of water-dispersible-powder were obtained.

Example Chemical 3 (Granules)

    ______________________________________                                         Compound No. 192      5                                                        Bentonite             50                                                       Talc                  42                                                       Lignosulfonic acid soda                                                                              2                                                        Polyoxyethylenealkylaryl ether                                                                       1                                                        ______________________________________                                    

The foregoing materials were mixed sufficiently, and water is added in an adequate quantity as to be kneaded. Then, an extruding granulator was used, so that 100 parts of granule were obtained.

Example Chemical 4 (Flowable Agent)

    ______________________________________                                         Compound No. 361          30                                                   Sulfosuccinate di-2-ethylhexylester sodium salt                                                          2                                                    Polyoxyethylenenonylphenylether                                                                          3                                                    Antifoaming agent         1                                                    Propylene glycol          5                                                    Water                     59                                                   ______________________________________                                    

The foregoing materials were crushed and uniformly mixed by using a wet-type ball mill, so that 100 parts of flowable agent were obtained.

[Efficiency Test Examples of The Fungicide]

Effects of preventing and curing crop damage obtainable from the fungicide according to the present invention will now be specifically described.

The compound according to the present invention and the fungicide containing same have excellent effects in preventing and curing the following various crop diseases caused from Oomycetes: grape downy mildew (Plasmopara viticola), gourd downy mildew (Pseudoperonospora cubensis), damping-off type disease (Phytophthora melonis), phytophora blight (Phytophthora capsici), late blight (Phytophthora infestans), rape vegetable downy mildew (Peronospora brassicae), Welsh onion downy mildew (Peronospora destructor), spinach downy mildew (Peronospor spinaciae), soybean downy mildew (Peronospora manshurica), broad bean downy mildew (Peronospora viciae), tobacco disease (Phytophthora nicotiana var. nicotiana), potato disease (Phytophthora infestaris), hop disease (Pseudoperonospora humuli), pineapple disease (Phytophthora cinnamomi), green pepper disease (Phytophthora capsici), strawberry root rot (Phytophthora fragarie) and various damping-off type diseases (caused from Pythium group germs).

The results of the following tests were evaluated in such a manner that the degree of crop damages were examined in accordance with the following reference seven days after the inoculation of disease-causing germs and the severity and the preventive value were obtained by the following equations.

    ______________________________________                                         Evaluation   Degree of Disease                                                 ______________________________________                                         Excellent    No disease found                                                  Good         Lesion area was less than 1/3                                     Allowable    Lesion area was 1/3 to less than 2/3                              No Good      Disease area was 2/3 or more                                      ______________________________________                                          ##STR19##                                                                     -   where                                                                 

n⁰ : No of leaves in which the degree of disease was Excellent

n¹ : No of leaves in which the degree of disease was Good.

n² : No of leaves in which the degree of disease was Allowable

n³ : No of leaves in which the degree of disease was No Good.

N: n⁰ +n¹ +n² +n³ ##EQU1##

The test results were evaluated in accordance with the following criteria.

    ______________________________________                                         Criteria                                                                       ______________________________________                                         A:       Preventive value was 95% or higher                                    B:       Preventive value was 80% to lower than 95%                            C:       Preventive value was 50% to lower than 80%                            D:       Preventive value was lower than 50%                                   ______________________________________                                    

Test Example 1

Test to evaluate the effect of preventing cucumber downy mildew

Five seeds of cucumber (variety: Sagami Hanshiro) were seeded in vinyl chloride pots each having a diameter of 9 cm and cultivated in a greenhouse for seven days. The water-dispersible powder according to Example Chemical 2 was diluted with water to obtain a concentration of effective component of 200 ppm, 10 ml of this was sprayed on each seedling of cucumbers having spread cotyledons. One day after spraying, a globule suspension of cucumber downy mildew (Pseudoperonospora cubensis) was inoculated by atomization. The seedlings were allowed to stand in a wet room at 20° C. for one day. Then, the seedlings were transferred and Brown in a greenhouse so as to observe the degree of disease. The results of the evaluations are shown in Table 13.

                  TABLE 13                                                         ______________________________________                                         Compound No.                                                                               Grade     Compound No.                                                                               Grade                                        ______________________________________                                          1          A         301         A                                             37         A         310         A                                             41         B         312         A                                             49         A         314         A                                             59         A         337         A                                             61         A         339         A                                             83         B         341         A                                             89         B         357         A                                            101         A         359         A                                            124         A         361         A                                            192         A         363         B                                            206         A         389         D                                            216         A         492         C                                            284         B         502         D                                            294         A         610         B                                            ______________________________________                                    

Test Example 2

Test to evaluate the effect of preventing potato disease

The water-dispersible powder according to Example Chemical 2 was diluted with water to obtain a concentration of effective component of 200 ppm and 10 ml of this was sprayed on each leaf of the potatoes (variety: Meikuin). One day after spraying, a globule suspension of potato disease (Phytophthora infestans) was inoculated by atomization. The seedlings were allowed to stand in a wet room at 17° C. for one day. Then, the seedlings were transferred and grown in a greenhouse so as to observe the degree of disease. The results of the evaluations are shown in Table 14.

                  TABLE 14                                                         ______________________________________                                         Compounds No.   Evaluation                                                     ______________________________________                                          61             A                                                              206             A                                                              ______________________________________                                    

(Effect of the Invention)

The compound expressed by general formula (I) is characterized by a structure in which the specific aryl group is bonded to the 1-sulfamoyl-1,2,4-triazole ring while interposing the sulfonyl group. The characterized structure is considered to cause the sulfamoyltriazole derivative to exhibit the excellent fungicidal performance. 

What is claimed is:
 1. A sulfamoyltriazole derivative expressed by formula (I): ##STR20## in which R¹ and R² are the same or different lower alkyl groups or an alkylene chain formed by integrating R¹ and R² and having 3 to 6 carbon atoms which may be substituted by a lower alkyl group; l is 1; and A is expressed by any one of the following substituents: ##STR21## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is an integer 1, 2, 3, 4 or 5, Y is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; n is an integer 1, 2, 3, 4 or 5; R³ and R⁴ are the same or different hydrogen atoms or lower alkyl groups; and p is an integer 1, 2, 3 or
 4. 2. A sulfamoyltriazole derivative according to claim 1 wherein A is expressed by any one of the following substituents: ##STR22## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is an integer 1, 2, 3, 4 or 5, Y is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; n is an integer 1, 2, 3, 4 or 5; and R³ and R⁴ are the same or different hydrogen atoms or lower alkyl groups.
 3. A sulfamoyltriazole derivative according to claim 1 wherein A in formula (I) is expressed by the following formula: ##STR23## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is an integer 1, 2, 3, 4 or
 5. 4. A fungicidal composition containing a sulfamoyltriazole derivative expressed by formula (I) as an effective component: ##STR24## in which R¹ and R² are the same or different lower alkyl groups or an alkylene chain formed by integrating R¹ and R² and having 3 to 6 carbon atoms which may be substituted by a lower alkyl group; l is 0; and A is expressed by any one of the following substituents: ##STR25## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is 1, 2, 3, 4 or 5, Y is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; n is 1, 2, 3, 4 or 5; R³ and R⁴ are the same or different hydrogen atoms or lower alkyl groups; and p is 1, 2, 3 or 4 together with an agriculturally acceptable carrier, diluent, additive and/or adjuvant.
 5. A fungicidal composition according to claim 4 wherein l in formula (I) is 1 and A is expressed by any one of the following substituents: ##STR26## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is an integer 1, 2, 3,4 or 5, Y is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; n is an integer 1, 2, 3, 4 or 5; and R³ and R⁴ are the same or different hydrogen atoms or lower alkyl groups.
 6. A fungicidal composition according to claim 4 wherein A in formula (I) is expressed by the following formula: ##STR27## in which X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkylcarbonyl group, a phenyl group, a phenoxy group, a benzyl group, a benzyloxy group, a formyl group, a lower alkoxycarbonyl group, a nitro group, a cyano group or an acetylamino group; m is an integer 1, 2, 3, 4 or
 5. 7. A sulfamoyltriazole derivative according to claim 1, which is 1-dimethylsulfamoyl-3-(2,4-dichloro-3-methylphenoxysulfonyl)-1,2,4-triazole.
 8. The composition as claimed in claim 4, wherein the sulfamoyltriazole derivative of formula (1) is present in a fungicidally effective amount. 